Polypropylene fibers dyed with 4-nitroacridone dyes



3,188,164 POLYPROPYLENE FIBERS DYED WITH 4-NITROACRIDONE DYES Joseph W. Dehn, Jr., Great Neck, and Harold J. Kuhefuss,

United States Patent,

. Patented June 8, 1965 "ice The test pieces were all examined at 20-hour intervals up to 80 hours. Changes were noted, at least until a distinct break occurred. Lightfastness tests were made in the conventional way on the Fade-O-Meter.

Brooklyn, N.Y and John J. Maituer, Hazlet, N .J., and The preparation of the dimethoxy-4-nitroacridone dyes Auth9ny Salma, New York, to t i described in application Serial No. 152,670, filed No g g figg 'p New York, -i a corporahon vember 15, 1961. The preparation of 5-1nethy1thio-4- nitroacridone (S-methyhnercapto-4-nitroacridone) is de- Drawing Filed 1963 253040 scribed in application Serial No. 237,394, filed November 6 Claims. (Cl. 8-55) I 10 13 1962 This invention relates to polypropylene fibers dyed Marasperse N is a ligno sulfonate. with 4-nitroarcridone dyes. Cyclopon AF is sodium N-acyl-N- methyhtaurate. It has been found that 4-nitroacridone and some of Sulframin AB is sodium alkyl-benzene-sulfonate. its derivatives act as disperse dyes for polypropylene What is claimed is: fibers when applied by more or less conventional means. 15 1. Polypropylene fiber dyed with a 4-nitroacridone dye The dyes display much better lightfastness when dyed selected from the group consisting of on polypropylene fibers than do the commercially avail- (a) a compound having the formula able dyes recommended by the fiber manufacturers,

The detailed procedure that followsillustrates a specific embodiment of this invention.

EXAMPLE A mixture of 3.00 g. of the dye, 1.00 g. of Marasperse N, and 1.00 g. of Cyclopon AF was combined with water 1 and ground with a hand muller to disperse the dye. After h R 1 d f h f H the material was oven dried, it was ground to a powder W erem Se ecte group conslstmg o with mortar and pestle and used to make up the dyebath. and CHHO at leastfme R bemg A convenient weight of polypropylene fiber in the form 09) a compound havmg the formula of cloth was scoured minutes at 70 C. in an aqueous 0 R solution of 1% (based on fiber weight) of an anionic 30 I wetting agent such as Sulframin AB and 0.25% (based R- .R on fiber weight) of sodium carbonate, A dyebath was i made up having about 40 times the Weight of the fiber. The dyebath was simply Water containing 1% (based NE on fiber weight) of an anionic wetting agent such as N01 sulfl'amm AB and 1/2% (based on fiber Weight) of the wherein R is selected from the group consisting of iiged Tlheflfloth vlgastecrlltertedbat 501066 tecrnpferatuge 221x21 H, C1, and Br two of the RS being H,

6 ye a was ea 6 a a on or a on c a com ound havn th formula hours. To remove surface dye, the goods were then p I g e soaped 30 minutes at 70 C. in an aqueous solution of 40 about 2% sodium carbonate (based on fiber weight) and about 1% (based on fiber weight) of a suitable dispersing agent such as Sulframin AB. The goods were then rinsed and dried.

Another set of dyeings was made using a similar pro- I cedure but with 2% dyestuff instead of /a%.

The table below gives specific examples, showing the wheleln one R 15 H and the other R 15 a dyestuff used, its color on polypropylene fiber, and the 7-II1ethY1-4-I1itI0aefid0ne, and lightfastness. (e) 5-methylthio-4-nitroacridone.

Dyed polypropylene fiber Dyestuii Color Light iastness 4-nitroaeridone -1 Yellow No break at 80 hours. 2-methoxy-4-nitroacridone Noticeable break at 80 hours. 5-meth0xy-4-nitrnar-ridnne d N oticeable break at 40 hours. 7-methoxy-4-nih'oacridone No break at 80 hours. 2, fi-dimethoxyt-nitroacridone Orange Vefiy slight break at 40 hours; slight break at 80 OUIS. 2, 7-dhnethoxy-4-rutroacridone Mauve Very slight break at 20 hours; slight break at 40 hours; no additional break at hours; slight break at hours. 5, 7-djmethoxy-4-nitroasridone Pink Slight break st 80 hours. 5, 8-dimethoxy-4-nitroacridone do Distinct break at 20 hours. 6,7-(or 7, 8-)-dirnethoxy-4-nitroacridone do V ry slight break at 40 hours; slight break at 80 ours. l-chloro-t-nitroacridone Orange Very slight break at 20 hours; slight break at 40 hours; distinct break at 60 hours. 2Oh10r0-4-nitroacririnna '.dn Slihght break at 40 hours; noticeable break at 80 OUTS. 2-bromo-4-nitrnar-ridnna rlo Slight break at 40 hours; another slight break at 60 hours; another slight break at 80 hours. 7-bromo-4-nltroacridone Yellow Slight break st 60 hours; noticeable break at 80 OUTS. 7-methyl-4-nitmaoririnna dn Very slight break at 40 hours; slight break at 60 hours; another slight break at 80 hours. 5-methylthio-4-nitroaeridone do Very slight break at 20 hours; slight break at 40 hours; another slight break at 60 hours.

3 4 2. Polypropylene fiber dyed with a dye having the 4. Polypropylene fiber dyed with a dye having the formula formula i f 1? 15 I R 5 l) R \I/\ I I R N09 N02 wherein R is selected from the group consisting of H and 10 wherein R is H and the other R is CH O. CH O, at least one R being H. '5. Polypropylene fiber dyed with 7-methyl-4-nitro- 3. Polypropylene fiber dyed With a dye having the acridone. formula 6. Polypropylene fiber dyed with 5-methylthio-4- O R 15 nitroacridone. u R References Cited by the Examiner 1 UNITED STATES PATENTS 2,005,303 6/35 Spiegler et al. 260279 X NH 20 3,054,793 9/62 Howard et a1. 260 279 X N01 3,074,950 1/63 Deusche et al. 260-279 wherein R is selected from the group consisting of H, Cl, and Br, two of the Rs being H. NORMAN G. TORCHIN, Primary Examiner. 

1. POLYPROPYLENE FIBER DYED WITH A 4-NITROACRIDONE DYE SELECTED FROM THE GROUP CONSISTING OF (A) A COMPOUND HAVING THE FORMULA 